124620-52-6

Basic information

• Product Name: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester
• Synonyms: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester
• CAS NO: 124620-52-6
• Molecular Weight: 603.927
• Mol File: 124620-52-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester(124620-52-6)
• EPA Substance Registry System: N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester(124620-52-6)

Safety Data

• Hazardous Substances Data: 124620-52-6(Hazardous Substances Data)

Upstream product

• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 32159-21-0 Cbz-L-pGlu-OH 
• 5891-45-2 (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 90195-00-9 N-<(2,2,2-trichloroethoxy)carbonyl>-O-benzylhydroxylamine 
• 124620-51-5 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-5-hydroxypentanoate 

Downstream Products

• 89969-29-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 
• 124620-53-7 allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithinate 
• 124620-55-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 
• 124620-54-8 allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 124620-56-0 (N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl)-(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 
• 124650-79-9 Allyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 130761-77-2 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-seryl-1,4-dibenzyl-D-aspartate 
• 130761-72-7 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithinate 
• 130761-71-6 allyl N²-(3,5-dinitrobenzoyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 
• 130761-84-1 N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-4-hydroxyphenylglycine 
• 130761-74-9 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-L-serinate 
• 130761-82-9 benzyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-D-4-hydroxyphenylglycinate 
• 131618-21-8 (3S,6S)-3-<3-2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione 
• 131618-22-9 (3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-3-acetoxy-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione 

Relevant articles and documents

Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine

N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid.Reduction of 6 to 7 and treatment with N-(trichloroethoxy)carbonyl>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.